The Long Con…
How dark money, a judicial pipeline, and a populist vehicle captured America’s last check on power
“We want a Supreme Court which will do justice under the Constitution — not over it. In our courts we want a government of laws and not of men.” — Franklin D. Roosevelt, Fireside Chat, March 9, 1937
Roosevelt spoke those words while trying to pack the Supreme Court with loyalists who would stop striking down his New Deal legislation. He was not defending judicial independence. He was arguing that the Court had overstepped and needed to be brought to heel. The irony is worth sitting with, because the frustration he expressed is recognizable today. Roosevelt was angry at a Court that blocked what he believed the people wanted. Now a different set of Americans are angry at a Court that advances what a narrow faction of donors wanted. The institution at the center of both complaints is the same. The question of who controls it, and for whose benefit, has never gone away.
Nine justices, appointed for life so they would never have to answer to a mob or a donor, charged with one job above all others. Protect the Constitution. Defend the rights of people who cannot defend themselves through ordinary politics. Be the last check when every other check fails.
That was the idea. And for a period in American history, the Court actually lived up to it.
In 1954, a unanimous Supreme Court under Chief Justice Earl Warren declared in Brown v. Board of Education that racial segregation in public schools violated the Fourteenth Amendment. Warren, a Republican appointee chosen by Eisenhower, understood something essential about the moment. He knew a divided Court would give segregationists ammunition. So he spent months persuading every justice to join, including holdouts who wept when the decision was finally read. The ruling did not end racism in America. But it established, at the highest level of law, that the Constitution means what it says about equal protection. That was the Court doing its job.
The Warren Court went on to build a body of law that most Americans now take for granted. Miranda v. Arizona told police they had to inform suspects of their rights before interrogation. Gideon v. Wainwright guaranteed every criminal defendant a lawyer, even if they could not afford one. Loving v. Virginia struck down laws banning interracial marriage. Reynolds v. Sims enforced the principle that legislative districts had to represent roughly equal numbers of people. One person, one vote. These were not partisan decisions in the way we understand that word today. They were expansions of liberty and equality that applied to everyone, decided by justices appointed by both parties, rooted in the text and purpose of the Constitution.
Eisenhower reportedly called his appointment of Warren the biggest mistake of his presidency. That reaction tells you everything about what the Court was supposed to be. A president appoints a justice expecting loyalty. The justice, freed by lifetime tenure from political debts, follows the law instead. The system worked precisely because the justices were not beholden to the people who put them there.
So what happened?
The conservative legal movement that captured this Court did not emerge overnight. It was built deliberately over four decades by people who understood that controlling the judiciary was more efficient than winning elections. The story begins in 1982, when a small group of law students at Yale, Harvard, and the University of Chicago founded the Federalist Society. Their stated aim was to challenge what they saw as liberal dominance of legal academia and to promote originalism, the idea that the Constitution should be interpreted according to the meaning its words carried when they were written.
The intellectual case for originalism deserves to be taken seriously, because the people who corrupted it understood its appeal better than its critics did. The Warren Court’s expansion of rights was, in many cases, built on reasoning that stretched the text of the Constitution beyond what its authors demonstrably intended. Reasonable people could worry about where that approach might lead. If justices can read new rights into the Constitution whenever they believe justice demands it, what constrains them from reading in rights that reflect their own preferences rather than any democratic consensus? Originalism offered an answer. It said the Constitution means what it meant when it was ratified, and if you want it to mean something different, you amend it. That is a coherent theory of judicial restraint, and it attracted serious legal minds who believed in limiting the power of unelected judges.
But the Federalist Society was never just a debating club. It became, over the next forty years, the most powerful judicial pipeline in American history. It recruited conservative law students, mentored them, connected them to clerkships and government positions, and ultimately served as the unofficial vetting organization for Republican judicial appointments. By the time Donald Trump ran for president in 2016, the pipeline was so well established that he could openly promise his Supreme Court nominees would be chosen by the Federalist Society. He was not exaggerating. Leonard Leo, the organization’s longtime executive vice president, personally assembled the lists of potential nominees for Trump’s three Supreme Court picks and played a central role in the confirmations of John Roberts and Samuel Alito under George W. Bush.
The scale of the operation is worth pausing on. Senator Sheldon Whitehouse has documented how Leo orchestrated hundreds of millions of dollars in anonymous donations to influence judicial selection, flowing through a network of front groups and dark money vehicles. In 2021, a secretive Chicago electronics magnate named Barre Seid transferred his entire company to a nonprofit controlled by Leo, a transaction worth $1.6 billion and likely the largest political donation in American history. The structure of the transfer allowed Seid to avoid an estimated $400 million in capital gains taxes. This was not a grassroots movement. It was a coordinated, lavishly funded campaign by corporate and ideological interests to install judges who would deliver specific outcomes.
The donor class behind this project had a problem. They had the money. They had the legal infrastructure. They had the Federalist Society pipeline and the dark money networks and Leonard Leo’s contacts. What they did not have was a mass political constituency. The things these donors wanted most, gutting environmental regulation, weakening labor protections, shielding corporations from accountability, eliminating campaign finance restrictions, are not popular positions. You cannot win a national election by telling voters you want to make it easier for chemical companies to dump waste in their rivers. You need a vehicle. You need someone who can mobilize the very people whose interests you are working against and convince them that your project is their project.
Donald Trump was that vehicle.
The relationship between Trump and the conservative donor network was transactional from the start. Charles Koch initially refused to support Trump in 2016. The two camps were openly hostile. But they reached an accommodation built on a simple exchange. Trump would outsource judicial selection entirely to the Federalist Society and Leonard Leo. In return, the donor network would look past everything about Trump that offended their stated principles, the protectionism, the chaos, the vulgarity, because he was delivering the one thing they could not get from a more conventional Republican. He could fill arenas with working class voters who would never in their lives attend a Federalist Society gala, voters who had no idea what Chevron deference meant or why anyone would spend $1.6 billion to overturn it, but who would pull the lever for Trump because he told them he was fighting for them.
For decades, the conservative legal project had been an elite enterprise with enormous intellectual infrastructure but almost no popular mandate. The regulatory rollbacks and corporate protections it pursued would benefit shareholders and executives while doing nothing for, and often actively harming, the working people in places like Beaver County. Trump solved that problem. He brought the crowds. He brought the loyalty of millions of people who had been left behind by the very economic system the donors were trying to protect from regulation. Leonard Leo, at a private meeting with Koch network financiers at the Broadmoor resort in Colorado Springs in the summer of 2018, personally assured the room that the Kavanaugh nomination was just the beginning. Senator John Cornyn told the same gathering that the Senate planned to fill every appellate vacancy it could before the end of the year. According to exit polls from 2016, one in five voters cited the Supreme Court as a reason they voted. Among those who called it the most important factor, 56 percent chose Trump. The Court vacancy Mitch McConnell had manufactured by blocking Merrick Garland was not just a constitutional violation. It was a voter mobilization tool.
The result is a Court built by donors who wanted deregulation, installed through a process engineered by operatives who wanted ideological control, and legitimized by voters who wanted something else entirely. The working people who sent Trump to the White House because he promised to drain the swamp got a Supreme Court that overturned Chevron, which means the swamp is now being drained of the regulators who protected their air and water and workplace safety. They got a Court that gutted campaign finance restrictions in Citizens United, which means the donors who orchestrated this project can now spend even more freely and even more secretly. They got a Court that weakened the Voting Rights Act in Shelby County v. Holder, which means the channels through which they might correct any of this at the ballot box have been narrowed.
I want to say this clearly. The conservative donor class did not stumble into Trump. They made a calculated bet. They looked at a man who could command the passionate loyalty of the very people whose economic interests the donor class was systematically undermining, and they saw an opportunity that might not come again. They moved on it with speed, precision, and an enormous amount of money. Three Supreme Court seats in four years. According to Senator Whitehouse, 86 percent of Trump’s first term circuit and Supreme Court nominees were affiliated with the Federalist Society. A six to three supermajority that will shape American law for a generation. If you are Leonard Leo, sitting on $1.6 billion in dark money, the investment has already paid for itself many times over.
But the capture of the Court required more than money and a popular vehicle. It required a willingness to break the norms that had governed judicial appointments for generations. That moment came in February 2016, when Justice Antonin Scalia died and Senate Majority Leader Mitch McConnell announced, within hours, that President Obama would not be permitted to fill the vacancy. Obama nominated Merrick Garland, a moderate appellate judge who had been confirmed to his existing seat with broad bipartisan support. The eleven Republican members of the Senate Judiciary Committee signed a letter refusing to hold hearings on any nominee. No proceedings of any kind were held. Garland’s nomination expired after 293 days, the longest pending period for any Supreme Court nominee in history. It was the first time in over a century that a nominee whose name had not been withdrawn was denied any consideration for an open seat.
McConnell later called this the proudest moment of his career. When Ruth Bader Ginsburg died in September 2020, just weeks before a presidential election, McConnell reversed his own stated principle and pushed Amy Coney Barrett’s confirmation through in thirty days. Senator Lindsey Graham had said in 2016, on camera, that if a Republican president faced the same situation, he should be held to the same standard. He asked people to use his words against him. They did. It did not matter. The real message was simpler. Power is its own justification. Norms exist until they become inconvenient.
The result is a Court that looks nothing like the institution the founders envisioned or the one Americans came to trust during the civil rights era. Six justices, all appointed by Republican presidents, all affiliated with the Federalist Society, now form a reliable conservative supermajority. Three justices appointed by Democratic presidents dissent. On the cases that matter most to the conservative legal movement, the pattern is mechanical. The same six vote together. The same three object. The outcomes arrive on schedule.
In Dobbs v. Jackson Women’s Health Organization, the Court overturned fifty years of precedent and eliminated the constitutional right to abortion. In New York State Rifle and Pistol Association v. Bruen, it expanded gun rights. In Students for Fair Admissions v. Harvard, it ended race conscious admissions. In Loper Bright v. Raimondo, it overturned the Chevron doctrine, stripping federal agencies of the deference courts had given them for forty years when interpreting ambiguous statutes. In United States v. Skrmetti, it upheld state bans on gender affirming care for minors, ruling six to three that the laws did not trigger heightened scrutiny under the Equal Protection Clause. In Mahmoud v. Taylor, it ruled six to three that parents have a constitutional right to opt their children out of school curricula featuring LGBTQ inclusive content on religious grounds. The pattern runs in one direction.
The question I keep coming back to is whether this is conservative or something else. Classical conservatism, in the tradition of Edmund Burke, means caution about rapid change, respect for established institutions, and skepticism of concentrated power. What this Court is doing looks different. Overturning a fifty year old constitutional right is not cautious. Stripping regulatory agencies of their authority while telling citizens to petition Congress, knowing full well that Congress is gridlocked by design, is not a defense of democratic self governance. It is a transfer of power from accountable institutions to an unelected body of nine. Sending abortion back to the states at the same time the Court has made it harder to challenge gerrymandered maps and voting restrictions is not an invitation to democratic participation. It is a trap.
The Chevron decision is the clearest example of this dynamic. For four decades, when a federal statute was ambiguous, courts deferred to the expert agency Congress had charged with implementing it. The Environmental Protection Agency interpreted environmental law. The Securities and Exchange Commission interpreted securities law. The reasoning was straightforward. Congress writes broad statutes because it cannot anticipate every situation. The agencies staffed with scientists, economists, and subject matter experts are better positioned than federal judges to fill in the details. By eliminating that deference, the Court did not return power to Congress. Congress still writes the same broad statutes. What changed is that federal judges, who are not experts in anything except law, now substitute their own judgment for the judgment of the people who actually understand the regulatory questions at hand. The practical effect is that regulated industries can challenge any rule they dislike in court, before judges who may have no background in the relevant science or economics, and win.
A conservative Court would restrain itself. It would respect precedent. It would be wary of concentrating too much power in any single institution, including its own. What we have instead is a Court that has systematically expanded its own authority while shrinking the authority of every other institution it touches. Federal agencies lose deference. States gain power over individual rights, but only the rights this particular majority is comfortable discarding. The channels for democratic correction, voting rights, campaign finance reform, redistricting, have been narrowed by the same Court that tells dissatisfied citizens to use democracy to fix what they do not like.
The Federalist Society provided the intellectual architecture and the personnel pipeline. Leonard Leo and his network of anonymous donors provided the money. Mitch McConnell provided the raw political will to break norms that had held for over a century. Donald Trump provided the popular constituency, millions of working class voters who had no stake in deregulation or corporate liability shields but who trusted him when he said he was fighting the establishment. And originalism, the theory that began as a legitimate call for judicial humility, provided the intellectual veneer for reaching outcomes the movement wanted all along, outcomes that lack majority support and could never be achieved through legislation. Dark money flows on both sides of American politics, through vehicles like the Arabella Advisors network on the left and the Koch and Leo networks on the right. But the scale, the coordination, and the singular focus on capturing an entire branch of government distinguish the conservative legal project from anything its counterparts have attempted.
The deeper problem is legitimacy. The Supreme Court has no army. It has no budget to speak of. Its authority rests entirely on the public’s belief that it is acting in good faith, interpreting the law rather than imposing a political program. When six justices appointed through a process shaped by one political faction, funded by anonymous donors, and installed through norm breaking maneuvers consistently deliver the outcomes that faction wants, that belief erodes. The institution that once commanded reverence from people like my family in Beaver County, people who did not follow legal theory but trusted that the system was fair, is losing the one thing it cannot function without.
The Warren Court was not perfect. Its critics accused it of overreach, of substituting its own moral convictions for the text of the Constitution, and some of those criticisms fed the very movement that would eventually capture the Court in the name of restraint. But the Warren Court was reaching toward something. It was trying to make the promise of equal protection real for people who had been excluded from it. The direction was outward, toward more liberty, more equality, more participation in the democratic project.
The current Court is reaching in the opposite direction. Inward, toward a narrower conception of who the Constitution protects and what the government can do on behalf of its citizens. It is consolidating power in the judiciary while dismantling the tools ordinary people use to hold their government accountable.
And the Court was only the beginning. While it cleared the legal obstacles, the Heritage Foundation and its network of conservative organizations were building something even more ambitious. They called it Project 2025, a 922 page blueprint for restructuring the entire executive branch of the federal government, written by hundreds of conservative operatives, nearly half of the collaborating organizations funded through Leonard Leo’s dark money network. The plan called for replacing tens of thousands of career civil servants with ideological loyalists, gutting regulatory agencies, dismantling environmental protections, and concentrating unprecedented power in the presidency. It was not a set of policy suggestions. It was an instruction manual for authoritarian governance, drafted in plain sight and published more than a year before the 2024 election.
Trump told the country he had never heard of it. “I know nothing about Project 2025,” he posted on Truth Social in July 2024. “I have no idea who is behind it.” This was a lie so transparent it barely qualifies as one. At least 140 people who worked in his first administration helped write the thing. Six of his former Cabinet secretaries contributed. His own running mate wrote the foreword to the Heritage Foundation president’s book. In April 2022, Trump had stood at a Heritage Foundation dinner and told the room they were “going to lay the groundwork and detail plans for exactly what our movement will do” when they returned to power. He knew. He always knew. But the voters who cheered for him at rallies in swing states did not know, and that was the point.
Within days of taking office in January 2025, the mask came off. A TIME analysis found that nearly two thirds of Trump’s initial executive orders mirrored or partially mirrored proposals from Project 2025. By the one year mark, the Center for Progressive Reform documented that the administration had initiated or completed 53 percent of the blueprint’s domestic policy agenda. The people who wrote it were appointed to implement it. Russell Vought, who authored the Project 2025 chapter on the Executive Office, was nominated to lead the Office of Management and Budget. Brendan Carr, who wrote the chapter on the Federal Communications Commission, was nominated to run it. The Heritage Foundation’s president, Kevin Roberts, declared that the organization’s role was to “institutionalize Trumpism.” This was not governance. It was an installation.
The people who voted for Trump because they were angry about their grocery bills, about fentanyl, about a country that seemed to have forgotten them, did not vote for any of this. They did not vote to strip the agencies that keep their water clean and their workplaces safe. They did not vote to replace career scientists and inspectors with political operatives whose only qualification was loyalty to one man. They did not vote to hand $1.6 billion in dark money influence over the structure of American democracy. They voted because a man who owned a gold plated penthouse in Manhattan looked into a camera and told them he understood their pain, and they believed him, because the resentment was real even if the messenger was not. He fed that resentment the way a con artist feeds trust. He gave it language, gave it targets, gave it the energy of a movement. And while the crowds roared, the operatives behind him quietly executed a plan to remake the government in ways that will harm the very people who put him there for a generation.
That is the transaction at the heart of this story. Not Trump and the donors. That deal was straightforward. The deeper transaction was between Trump and the tens of millions of Americans who traded their democratic leverage for the feeling of being heard. They were not heard. They were used. Their passion was converted into judicial appointments, regulatory rollbacks, and the installation of an authoritarian policy framework that no candidate could have won an election by honestly describing. The conservative movement did not persuade the public to support Project 2025. A poll by NBC in September 2024 found that just seven percent of registered Republicans viewed the plan positively. So they hid it behind a populist who promised to drain the swamp while filling it with ideologues who had been waiting decades for exactly this opportunity.
The donors saw it. The operatives planned it. The Federalist Society vetted the judges. The Heritage Foundation wrote the playbook. And Donald Trump sold it to people who never would have bought it if they had understood what they were purchasing.
When I was a kid and I heard others talk about the Supreme Court, they talked about it the way they talked about the church. It was a place where, when everything else failed, someone would do the right thing. That faith was not naive. For a period in American history, it was justified. What we have now is something different. The Court has been captured. The executive branch is being restructured by a blueprint the president pretended not to recognize. And the people whose resentment made it all possible are the ones who will pay the highest price for what comes next. Pretending otherwise is not respect for the institution. It is complicity in its transformation into something the founders would not recognize and should not have had to imagine.